Nonpolymeric thermosensitive benzenetricarboxamides.

ABSTRACT

A new class of nonpolymeric thermosensitive materials based on the benzene-1,3,5-tricarboxamide (BTC) structural platform are described. We observed that the benzocrown ether-substituted BTC derivatives undergo an unusual temperature-dependent reversible solubility change in aqueous solution. Thus, a clear nonfluorescent solution of BTC derivatives becomes turbid and generates fluorescent aggregates above the LCST temperature. The aggregates disappear, and a clear solution is reformed when the solution is cooled to 20 °C. It is believed that the LCST behavior of BTC derivatives results from the removal of water molecules from crown ether moieties at elevated temperature. Thus, BTC derivatives exist in fully hydrated forms below the LCST. Heating the BTC derivatives solutions causes the expulsion of water and induces the formation of aggregates. At room temperature, the removal of water from BTC derivatives occurs slowly and leads to the formation of long nanofibers.